Ethanol → 2-{1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-3-methyl-but-1-enyl}-5-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 1515836Notes

Reaction equation

HRID 1515836 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:20]([C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH2:34][CH2:35][O:36][CH3:37])(=[O:33])=[O:32])=[CH:27][CH:26]=2)=[CH:21][CH:22]([CH3:24])[CH3:23])(=O)=O)C=CC=CC=1.[OH-].[Na+].[CH2:40](O)C>O1CCCC1.ClCCl>[CH2:37]([O:36][CH2:35][CH2:34][S:31]([C:28]1[CH:29]=[CH:30][C:25]([C:20]([C:11]2[NH:10][C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=2)=[CH:21][CH:22]([CH3:23])[CH3:24])=[CH:26][CH:27]=1)(=[O:33])=[O:32])[CH3:40]

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 672285511-benzenesulfonyl-5-fluoro-2-{1-[4-(2-methoxy-ethanesulfonyl)-phenyl]-3-methyl-but-1-enyl}-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 672289872-{1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-3-methyl-but-1-enyl}-5-fluoro-1H-pyrrolo[2,3-b]pyridineYield 34%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-benzenesulfonyl-5-fluoro-2-{1-[4-(2-methoxy-ethanesulfonyl)-phenyl]-3-methyl-but-1-enyl}-1H-pyrrolo[2,3-b]pyridine (0.6 g, 1.1 mmol) in ethanol (8 mL), tetrahydrofuran (15 mL) and an aqueous sodium hydroxide solution (10%, 10 mL) was heated at 45° C. for 16 h. The mixture was diluted with dichloromethane (150 mL), washed with water, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 30% ethyl acetate/hexanes) afforded 2-{1-[4-(2-ethoxy-ethanesulfonyl)-phenyl]-3-methyl-but-1-enyl}-5-fluoro-1H-pyrrolo[2,3-b]pyridine (160 mg, 34%): LC/MS m/e calcd for C22H25FN2O3S [M+H]+ 417.52, observed 416.8.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company, 30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-368f3f73e5834d3ca6fec5f193239aaf
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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